Stereoselective Direct N-Trifluoropropenylation of Heterocycles with a Hypervalent Iodonium Reagent.

Abstract

The availability and synthesis of fluorinated enamine derivatives such as N‐(3,3,3‐trifluoropropenyl)heterocycles are challenging, especially through direct functionalization of the heterocyclic scaffold. Herein, a stereoselective N‐trifluoropropenylation method based on the use of a bench‐stable trifluoropropenyl iodonium salt is described. This reagent enables the straightforward trifluoropropenylation of various N‐heterocycles under mild reaction conditions, providing trifluoromethyl enamine type moieties with high stereoselectivity and efficiency.